Pros
In the same way that Salesforce is the control center for customer data, Rippling is quickly doing the same for all things employee data. The product is amazing and is truly differentiated from everything else in the market. They're innovating across every area of the product and the roadmap around AI, data cloud, and solutions is making the product stickier as it automates more and more business processes for customers. The SF HQ is also a joy to work at. It has become the beating heart of the FiDi as most tech companies are across Market St. and most of the traditional FiDi is filled with legacy Finance companies. They've committed to SF and are continuing to expand their presence. Sales Leadership is also a great group that genuinely care about and support their employees' development + career goals. The expectations are high given their consistent success, but there's a real opportunity to make life-changing commissions and the base is very competitive. Also, given ~67% of reps in Mid-Market were above 100% in FY '25, the OTE is very realistic. The in-person mandate (3 days/wk) is more flexible than most hypergrowth companies and for parents they are very understanding of the demands of commuting and daycare dropoff/pickup. You get 4 "Work from Anywhere" weeks in addition to "Work from Home Sick days" as well. They're >5,100 employees, so the equity isn't as compelling as it was for early employees, but you still get RSU's in a compound startup with a very predictable revenue engine that should continue to skyrocket in value.
Cons
Like any successful + large company, there's a lot of red tape to jump through (e.g. CPQ can be slow) and processes to follow, but they are investing a lot in automation to ease the burden. Having captured the majority of the market share in their ICP (tech), Rippling is pushing hard into the traditional economy. There are some nuanced feature gaps that they're working quickly to fill, but the result is you run into a lot of companies who are looking for a simple, inexpensive payroll solution and aren't drawn to the brand or unification story that set Rippling apart. You're also at the mercy of the round-robin system and your book of accounts (there are ~60 reps in Core MM), so you can expect to take a good amount of calls where the prospeect is just looking to learn more about Rippling and isn't actively looking to implement a new HR & Payroll platform. The key is to focus on the accounts that are a good fit & are gravitating toward the value that Rippling provides. You can often hit your number with just a few large deals each quarter with a couple smaller deals sprinkled in. You can lose your target accounts if the Broker team is introduced through a partner or if the company wants to just purchase 1 (or a small #) of EOR seats and elects to wait to make the broader HRIS + Payroll transition.